# Supplementary Information (SI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_05
_database_code_depnum_ccdc_archive 'CCDC 2380263'
loop_
_audit_author_name
_audit_author_address
'Zhengzheng Zhou'
;Southern Medical University
China
;
_audit_update_record             
;
2024-08-28 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_date             2024-08-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'C9 H8 Cl2 N5, C13 H8 F3 N2 O2, 2(C2 H6 O)'
_chemical_formula_sum            'C26 H28 Cl2 F3 N7 O4'
_chemical_formula_weight         630.457
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.01788 0.00908 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
Cl 0.36457 0.70364 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.07327 0.05351 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.03110 0.01806 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.04960 0.03234 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   10.7304(9)
_cell_length_b                   11.1991(9)
_cell_length_c                   12.3605(8)
_cell_angle_alpha                93.057(6)
_cell_angle_beta                 96.405(6)
_cell_angle_gamma                99.535(7)
_cell_volume                     1451.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3441
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      74.0740
_cell_measurement_theta_min      3.9710
_exptl_absorpt_coefficient_mu    2.584
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.41976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_description       prism
_exptl_crystal_F_000             655.857
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0528
_diffrn_reflns_Laue_measured_fraction_full 0.9973
_diffrn_reflns_Laue_measured_fraction_max 0.9547
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9771
_diffrn_reflns_point_group_measured_fraction_full 0.9973
_diffrn_reflns_point_group_measured_fraction_max 0.9547
_diffrn_reflns_theta_full        67.6840
_diffrn_reflns_theta_max         74.68
_diffrn_reflns_theta_min         3.61
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9973
_diffrn_measured_fraction_theta_max 0.9547
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -63.00  34.00   1.00    1.00    --  -40.73  38.00  30.00   97
  2  ω     21.00  77.00   1.00    1.00    --   40.73 -99.00  30.00   56
  3  ω     25.00  85.00   1.00    1.00    --   40.73-125.00 -60.00   60
  4  ω     51.00 115.00   1.00    1.00    --  108.83 -61.00  60.00   64
  5  ω     88.00 116.00   1.00    1.00    --  108.83-125.00 -30.00   28
  6  ω     39.00  77.00   1.00    1.00    --  108.83-125.00 -30.00   38
  7  ω     29.00  84.00   1.00    1.00    --  108.83 -95.00  30.00   55
  8  ω     45.00 122.00   1.00    1.00    --  108.83-125.00 120.00   77
  9  ω     34.00 134.00   1.00    1.00    --  108.83 -30.00 150.00  100
 10  ω     82.00 113.00   1.00    1.00    --  108.83  30.00  30.00   31
 11  ω    110.00 137.00   1.00    1.00    --  108.83 110.00 113.00   27
 12  ω    105.00 169.00   1.00    1.00    --  108.83 125.00  90.00   64
 13  ω     80.00 178.00   1.00    1.00    --  108.83  61.00-180.00   98
 14  ω     65.00 119.00   1.00    1.00    --  108.83 -77.00-180.00   54
 15  ω     58.00  94.00   1.00    1.00    --  108.83 -95.00-180.00   36
 16  ω     32.00 150.00   1.00    1.00    --  108.83 -15.00   0.00  118
 17  ω    -66.00  32.00   1.00    1.00    --  -40.73  57.00-120.00   98
 18  ω   -111.00 -17.00   1.00    1.00    --  -40.73 -57.00  90.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0282273000
_diffrn_orient_matrix_UB_12      -0.1165505000
_diffrn_orient_matrix_UB_13      0.0512634000
_diffrn_orient_matrix_UB_21      -0.0268865000
_diffrn_orient_matrix_UB_22      0.0510576000
_diffrn_orient_matrix_UB_23      0.1116297000
_diffrn_orient_matrix_UB_31      -0.1414061000
_diffrn_orient_matrix_UB_32      -0.0580605000
_diffrn_orient_matrix_UB_33      -0.0269389000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              12
_reflns_limit_h_min              -13
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                4304
_reflns_number_total             5684
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.4336
_refine_diff_density_min         -0.7704
_refine_diff_density_rms         0.1052
_refine_ls_d_res_high            0.7993
_refine_ls_d_res_low             12.2503
_refine_ls_goodness_of_fit_ref   1.0501
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    44
_refine_ls_number_parameters     389
_refine_ls_number_reflns         5684
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0837
_refine_ls_R_factor_gt           0.0669
_refine_ls_restrained_S_all      1.0501
_refine_ls_shift/su_max          0.0008
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1106P)²+0.5556P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1820
_refine_ls_wR_factor_ref         0.2045
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C2S(H2Sa,H2Sb), C3S(H3Sa,H3Sb)
2.b Aromatic/amide H refined with riding coordinates:
 N4(H4a), C16(H16), C17(H17), C18(H18), N2(H2), C2(H2a), C3(H3), C4(H4),
 C7(H7), C9(H9), C10(H10), C11(H11)
2.c X=CH2 refined with riding coordinates:
 N6(H6a,H6b), N7(H7a,H7b)
2.d Idealised Me refined as rotating group:
 C1S(H1Sa,H1Sb,H1Sc), C4S(H4Sa,H4Sb,H4Sc)
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Cl1 Cl 0.91227(9) 0.24005(9) -0.04758(7) 0.0581(3) Uani 1.000000 .
Cl2 Cl 0.92512(8) 0.45690(7) 0.12831(7) 0.0446(2) Uani 1.000000 .
N3 N 0.6240(2) 0.4615(2) 0.2962(2) 0.0365(6) Uani 1.000000 .
N4 N 0.6252(2) 0.5456(2) 0.3788(2) 0.0385(6) Uani 1.000000 .
H4a H 0.5551(2) 0.5751(2) 0.3854(2) 0.0462(7) Uiso 1.000000 R
N5 N 0.8342(2) 0.5369(2) 0.4527(2) 0.0360(6) Uani 1.000000 .
N6 N 0.7240(3) 0.6779(2) 0.5218(2) 0.0443(7) Uani 1.000000 .
H6a H 0.6547(3) 0.7105(2) 0.5206(2) 0.0531(8) Uiso 1.000000 R
H6b H 0.7904(3) 0.7062(2) 0.5701(2) 0.0531(8) Uiso 1.000000 R
N7 N 0.9334(2) 0.3924(2) 0.3794(2) 0.0400(6) Uani 1.000000 .
H7a H 0.9967(2) 0.4128(2) 0.4323(2) 0.0480(7) Uiso 1.000000 R
H7b H 0.9360(2) 0.3343(2) 0.3294(2) 0.0480(7) Uiso 1.000000 R
C14 C 0.8105(3) 0.3284(3) 0.1256(2) 0.0360(6) Uani 1.000000 .
C15 C 0.8025(3) 0.2341(3) 0.0458(3) 0.0419(7) Uani 1.000000 .
C16 C 0.7066(4) 0.1347(3) 0.0384(3) 0.0463(8) Uani 1.000000 .
H16 H 0.7032(4) 0.0699(3) -0.0153(3) 0.0555(10) Uiso 1.000000 R
C17 C 0.6156(4) 0.1295(3) 0.1092(3) 0.0474(8) Uani 1.000000 .
H17 H 0.5476(4) 0.0625(3) 0.1026(3) 0.0569(10) Uiso 1.000000 R
C18 C 0.6233(3) 0.2223(3) 0.1902(3) 0.0409(7) Uani 1.000000 .
H18 H 0.5606(3) 0.2181(3) 0.2390(3) 0.0491(8) Uiso 1.000000 R
C19 C 0.7217(3) 0.3211(3) 0.2001(2) 0.0351(6) Uani 1.000000 .
C20 C 0.7271(3) 0.4158(3) 0.2904(2) 0.0340(6) Uani 1.000000 .
C21 C 0.8347(3) 0.4491(3) 0.3752(2) 0.0337(6) Uani 1.000000 .
C22 C 0.7283(3) 0.5866(3) 0.4513(3) 0.0363(6) Uani 1.000000 .
F1 F 0.7824(3) -0.3059(2) 0.1645(3) 0.0877(9) Uani 1.000000 .
F2 F 0.7583(3) -0.1790(3) 0.0438(2) 0.0909(9) Uani 1.000000 .
F3 F 0.8928(2) -0.1297(2) 0.1868(2) 0.0732(7) Uani 1.000000 .
O1 O 0.5102(2) 0.2498(2) 0.4868(2) 0.0464(6) Uani 1.000000 .
O2 O 0.6065(2) 0.3915(2) 0.6150(2) 0.0438(5) Uani 1.000000 .
N1 N 0.8434(3) 0.0943(2) 0.4882(2) 0.0421(6) Uani 1.000000 .
N2 N 0.6279(2) 0.0767(2) 0.4271(2) 0.0412(6) Uani 1.000000 .
H2 H 0.5570(2) 0.1005(2) 0.4415(2) 0.0494(7) Uiso 1.000000 R
C1 C 0.7250(3) 0.2449(3) 0.5546(3) 0.0363(6) Uani 1.000000 .
C2 C 0.8326(3) 0.2988(3) 0.6227(3) 0.0398(7) Uani 1.000000 .
H2a H 0.8300(3) 0.3686(3) 0.6690(3) 0.0477(8) Uiso 1.000000 R
C3 C 0.9444(3) 0.2519(3) 0.6242(3) 0.0434(7) Uani 1.000000 .
H3 H 1.0185(3) 0.2879(3) 0.6716(3) 0.0521(9) Uiso 1.000000 R
C4 C 0.9448(3) 0.1514(3) 0.5546(3) 0.0467(8) Uani 1.000000 .
H4 H 1.0223(3) 0.1209(3) 0.5540(3) 0.0561(9) Uiso 1.000000 R
C5 C 0.7345(3) 0.1388(3) 0.4891(3) 0.0367(6) Uani 1.000000 .
C6 C 0.6100(3) -0.0174(3) 0.3451(3) 0.0382(7) Uani 1.000000 .
C7 C 0.7073(3) -0.0598(3) 0.2962(3) 0.0416(7) Uani 1.000000 .
H7 H 0.7941(3) -0.0295(3) 0.3222(3) 0.0500(9) Uiso 1.000000 R
C8 C 0.6747(3) -0.1471(3) 0.2089(3) 0.0447(8) Uani 1.000000 .
C9 C 0.5499(4) -0.1959(3) 0.1709(3) 0.0479(8) Uani 1.000000 .
H9 H 0.5300(4) -0.2561(3) 0.1115(3) 0.0575(10) Uiso 1.000000 R
C10 C 0.4541(4) -0.1552(3) 0.2213(3) 0.0467(8) Uani 1.000000 .
H10 H 0.3675(4) -0.1883(3) 0.1971(3) 0.0560(9) Uiso 1.000000 R
C11 C 0.4839(3) -0.0667(3) 0.3068(3) 0.0425(7) Uani 1.000000 .
H11 H 0.4173(3) -0.0390(3) 0.3400(3) 0.0510(9) Uiso 1.000000 R
C12 C 0.6050(3) 0.2983(3) 0.5521(3) 0.0377(7) Uani 1.000000 .
C13 C 0.7769(4) -0.1887(3) 0.1519(3) 0.0575(10) Uani 1.000000 .
O1S O 0.2523(3) -0.5664(3) 0.2303(3) 0.0658(8) Uani 1.000000 .
H1S H 0.297(5) -0.527(5) 0.272(4) 0.072(16) Uiso 1.000000 .
C1S C 0.3767(5) -0.5254(6) 0.0811(4) 0.0812(14) Uani 1.000000 .
H1Sa H 0.3739(16) -0.493(3) 0.0091(15) 0.122(2) Uiso 1.000000 GR
H1Sb H 0.4475(6) -0.478(3) 0.1303(18) 0.122(2) Uiso 1.000000 GR
H1Sc H 0.389(2) -0.6101(7) 0.074(3) 0.122(2) Uiso 1.000000 GR
C2S C 0.2596(5) -0.5195(5) 0.1244(4) 0.0773(13) Uani 1.000000 .
H2Sa H 0.1888(5) -0.5655(5) 0.0726(4) 0.0928(16) Uiso 1.000000 R
H2Sb H 0.2475(5) -0.4337(5) 0.1295(4) 0.0928(16) Uiso 1.000000 R
O2S O 1.0839(3) 0.2496(2) 0.2828(2) 0.0486(6) Uani 1.000000 .
H2S H 1.129(4) 0.298(4) 0.264(3) 0.044(13) Uiso 1.000000 .
C3S C 1.0819(5) 0.1327(4) 0.2301(4) 0.0724(14) Uani 1.000000 .
H3Sa H 1.0138(5) 0.0740(4) 0.2556(4) 0.0869(16) Uiso 1.000000 R
H3Sb H 1.0607(5) 0.1363(4) 0.1504(4) 0.0869(16) Uiso 1.000000 R
C4S C 1.2039(5) 0.0885(4) 0.2509(5) 0.0848(16) Uani 1.000000 .
H4Sa H 1.1971(14) 0.0087(18) 0.212(3) 0.127(2) Uiso 1.000000 GR
H4Sb H 1.2717(9) 0.146(2) 0.225(3) 0.127(2) Uiso 1.000000 GR
H4Sc H 1.224(2) 0.082(4) 0.3294(6) 0.127(2) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C15 1.735(4) . ?
Cl2 C14 1.728(3) . ?
N3 N4 1.349(3) . ?
N3 C20 1.301(4) . ?
N4 H4a 0.8800 . ?
N4 C22 1.344(4) . ?
N5 C21 1.337(4) . ?
N5 C22 1.344(4) . ?
N6 H6a 0.8800 . ?
N6 H6b 0.8800 . ?
N6 C22 1.318(4) . ?
N7 H7a 0.8800 . ?
N7 H7b 0.8800 . ?
N7 C21 1.320(4) . ?
C14 C15 1.391(4) . ?
C14 C19 1.393(4) . ?
C15 C16 1.377(5) . ?
C16 H16 0.9500 . ?
C16 C17 1.378(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(5) . ?
C18 H18 0.9500 . ?
C18 C19 1.388(5) . ?
C19 C20 1.487(4) . ?
C20 C21 1.454(4) . ?
F1 C13 1.340(4) . ?
F2 C13 1.343(5) . ?
F3 C13 1.322(5) . ?
O1 C12 1.253(4) . ?
O2 C12 1.264(4) . ?
N1 C4 1.335(4) . ?
N1 C5 1.345(4) . ?
N2 H2 0.8800 . ?
N2 C5 1.365(4) . ?
N2 C6 1.397(4) . ?
C1 C2 1.380(4) . ?
C1 C5 1.427(4) . ?
C1 C12 1.504(4) . ?
C2 H2a 0.9500 . ?
C2 C3 1.386(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(5) . ?
C4 H4 0.9500 . ?
C6 C7 1.398(4) . ?
C6 C11 1.393(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.391(5) . ?
C8 C9 1.380(5) . ?
C8 C13 1.490(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.386(5) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(5) . ?
C11 H11 0.9500 . ?
O1S H1S 0.73(5) . ?
O1S C2S 1.442(6) . ?
C1S H1Sa 0.9800 . ?
C1S H1Sb 0.9800 . ?
C1S H1Sc 0.9800 . ?
C1S C2S 1.430(7) . ?
C2S H2Sa 0.9900 . ?
C2S H2Sb 0.9900 . ?
O2S H2S 0.72(4) . ?
O2S C3S 1.426(4) . ?
C3S H3Sa 0.9900 . ?
C3S H3Sb 0.9900 . ?
C3S C4S 1.477(6) . ?
C4S H4Sa 0.9800 . ?
C4S H4Sb 0.9800 . ?
C4S H4Sc 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 N3 N4 117.4(2) . . ?
H4a N4 N3 118.45(15) . . ?
C22 N4 N3 123.1(2) . . ?
C22 N4 H4a 118.45(17) . . ?
C22 N5 C21 117.0(2) . . ?
H6b N6 H6a 120.0 . . ?
C22 N6 H6a 120.0 . . ?
C22 N6 H6b 120.0 . . ?
H7b N7 H7a 120.0 . . ?
C21 N7 H7a 120.0 . . ?
C21 N7 H7b 120.0 . . ?
C15 C14 Cl2 120.2(3) . . ?
C19 C14 Cl2 120.1(2) . . ?
C19 C14 C15 119.6(3) . . ?
C14 C15 Cl1 120.7(3) . . ?
C16 C15 Cl1 118.5(3) . . ?
C16 C15 C14 120.8(3) . . ?
H16 C16 C15 120.2(2) . . ?
C17 C16 C15 119.7(3) . . ?
C17 C16 H16 120.15(19) . . ?
H17 C17 C16 119.94(19) . . ?
C18 C17 C16 120.1(3) . . ?
C18 C17 H17 119.9(2) . . ?
H18 C18 C17 119.8(2) . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.77(19) . . ?
C18 C19 C14 119.2(3) . . ?
C20 C19 C14 122.8(3) . . ?
C20 C19 C18 118.0(3) . . ?
C19 C20 N3 116.1(3) . . ?
C21 C20 N3 120.2(3) . . ?
C21 C20 C19 123.5(3) . . ?
N7 C21 N5 118.3(3) . . ?
C20 C21 N5 120.2(3) . . ?
C20 C21 N7 121.5(3) . . ?
N5 C22 N4 121.5(3) . . ?
N6 C22 N4 118.4(3) . . ?
N6 C22 N5 120.1(3) . . ?
C5 N1 C4 117.5(3) . . ?
C5 N2 H2 113.89(17) . . ?
C6 N2 H2 113.89(17) . . ?
C6 N2 C5 132.2(3) . . ?
C5 C1 C2 116.9(3) . . ?
C12 C1 C2 120.0(3) . . ?
C12 C1 C5 123.1(3) . . ?
H2a C2 C1 119.72(18) . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2a 119.72(19) . . ?
H3 C3 C2 121.02(19) . . ?
C4 C3 C2 118.0(3) . . ?
C4 C3 H3 121.02(19) . . ?
C3 C4 N1 124.2(3) . . ?
H4 C4 N1 117.90(19) . . ?
H4 C4 C3 117.90(19) . . ?
N2 C5 N1 118.1(3) . . ?
C1 C5 N1 122.9(3) . . ?
C1 C5 N2 119.0(3) . . ?
C7 C6 N2 125.2(3) . . ?
C11 C6 N2 115.8(3) . . ?
C11 C6 C7 118.9(3) . . ?
H7 C7 C6 120.62(19) . . ?
C8 C7 C6 118.8(3) . . ?
C8 C7 H7 120.6(2) . . ?
C9 C8 C7 122.3(3) . . ?
C13 C8 C7 119.6(3) . . ?
C13 C8 C9 118.1(3) . . ?
H9 C9 C8 120.8(2) . . ?
C10 C9 C8 118.5(3) . . ?
C10 C9 H9 120.8(2) . . ?
H10 C10 C9 119.8(2) . . ?
C11 C10 C9 120.3(3) . . ?
C11 C10 H10 119.8(2) . . ?
C10 C11 C6 121.2(3) . . ?
H11 C11 C6 119.4(2) . . ?
H11 C11 C10 119.4(2) . . ?
O2 C12 O1 123.6(3) . . ?
C1 C12 O1 118.6(3) . . ?
C1 C12 O2 117.8(3) . . ?
F2 C13 F1 105.8(3) . . ?
F3 C13 F1 105.1(3) . . ?
F3 C13 F2 106.8(4) . . ?
C8 C13 F1 112.1(4) . . ?
C8 C13 F2 112.2(3) . . ?
C8 C13 F3 114.2(3) . . ?
C2S O1S H1S 110(4) . . ?
H1Sb C1S H1Sa 109.5 . . ?
H1Sc C1S H1Sa 109.5 . . ?
H1Sc C1S H1Sb 109.5 . . ?
C2S C1S H1Sa 109.5 . . ?
C2S C1S H1Sb 109.5 . . ?
C2S C1S H1Sc 109.5 . . ?
C1S C2S O1S 114.5(4) . . ?
H2Sa C2S O1S 108.6(3) . . ?
H2Sa C2S C1S 108.6(3) . . ?
H2Sb C2S O1S 108.6(3) . . ?
H2Sb C2S C1S 108.6(3) . . ?
H2Sb C2S H2Sa 107.6 . . ?
C3S O2S H2S 114(3) . . ?
H3Sa C3S O2S 108.9(3) . . ?
H3Sb C3S O2S 108.9(2) . . ?
H3Sb C3S H3Sa 107.7 . . ?
C4S C3S O2S 113.2(4) . . ?
C4S C3S H3Sa 108.9(3) . . ?
C4S C3S H3Sb 108.9(3) . . ?
H4Sa C4S C3S 109.5 . . ?
H4Sb C4S C3S 109.5 . . ?
H4Sb C4S H4Sa 109.5 . . ?
H4Sc C4S C3S 109.5 . . ?
H4Sc C4S H4Sa 109.5 . . ?
H4Sc C4S H4Sb 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C15 C14 Cl2 3.5(3) . . . . ?
Cl1 C15 C14 C19 -179.6(2) . . . . ?
Cl1 C15 C16 C17 -177.8(3) . . . . ?
Cl2 C14 C15 C16 -175.8(2) . . . . ?
Cl2 C14 C19 C18 174.0(2) . . . . ?
Cl2 C14 C19 C20 -5.6(3) . . . . ?
N3 N4 C22 N5 -6.8(3) . . . . ?
N3 N4 C22 N6 172.9(3) . . . . ?
N3 C20 C19 C14 126.2(3) . . . . ?
N3 C20 C19 C18 -53.3(3) . . . . ?
N3 C20 C21 N5 -7.7(3) . . . . ?
N3 C20 C21 N7 170.8(3) . . . . ?
N4 C22 N5 C21 3.3(4) . . . . ?
N5 C21 C20 C19 178.6(3) . . . . ?
N7 C21 C20 C19 -2.9(4) . . . . ?
C14 C15 C16 C17 1.5(4) . . . . ?
C14 C19 C18 C17 2.2(3) . . . . ?
C14 C19 C20 C21 -59.8(3) . . . . ?
C15 C16 C17 C18 -2.3(4) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C17 C18 C19 C20 -178.2(3) . . . . ?
C18 C19 C20 C21 120.7(3) . . . . ?
F1 C13 C8 C7 114.7(3) . . . . ?
F1 C13 C8 C9 -66.4(4) . . . . ?
F2 C13 C8 C7 -126.5(3) . . . . ?
F2 C13 C8 C9 52.4(4) . . . . ?
F3 C13 C8 C7 -4.7(4) . . . . ?
F3 C13 C8 C9 174.1(3) . . . . ?
O1 C12 C1 C2 177.7(3) . . . . ?
O1 C12 C1 C5 -2.4(4) . . . . ?
O2 C12 C1 C2 -1.1(4) . . . . ?
O2 C12 C1 C5 178.8(3) . . . . ?
N1 C4 C3 C2 -2.0(4) . . . . ?
N1 C5 N2 C6 -12.6(4) . . . . ?
N1 C5 C1 C2 -2.9(4) . . . . ?
N1 C5 C1 C12 177.1(3) . . . . ?
N2 C5 C1 C2 174.7(3) . . . . ?
N2 C5 C1 C12 -5.2(4) . . . . ?
N2 C6 C7 C8 -174.4(3) . . . . ?
N2 C6 C11 C10 176.1(3) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C6 C7 C8 C9 -2.0(4) . . . . ?
C6 C7 C8 C13 176.8(3) . . . . ?
C6 C11 C10 C9 -0.8(4) . . . . ?
C7 C8 C9 C10 0.7(4) . . . . ?
C8 C9 C10 C11 0.7(4) . . . . ?


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.749
_oxdiff_exptl_absorpt_empirical_full_min 0.622
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_02-1222
_database_code_depnum_ccdc_archive 'CCDC 2380266'
loop_
_audit_author_name
_audit_author_address
'Zhengzheng Zhou'
;Southern Medical University
China
;
_audit_update_record             
;
2024-08-28 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_date             2024-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H8 Cl2 N5, C14 H10 Cl2 N O2'
_chemical_formula_sum            'C23 H17 Cl4 N6 O2'
_chemical_formula_weight         551.22
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.8844(5)
_cell_length_b                   13.7991(8)
_cell_length_c                   14.5572(4)
_cell_angle_alpha                105.074(4)
_cell_angle_beta                 91.002(3)
_cell_angle_gamma                99.969(4)
_cell_volume                     2456.06(19)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6053
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      72.4020
_cell_measurement_theta_min      3.1130
_shelx_estimated_absorpt_T_max   0.706
_shelx_estimated_absorpt_T_min   0.561
_exptl_absorpt_coefficient_mu    4.672
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.47548
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1124
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.08
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0641
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.967
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            17321
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.967
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.903
_diffrn_reflns_theta_min         3.151
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.967
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -28.00   0.00   1.00    1.00    --   40.73 -57.00 120.00   28
  2  ω      4.00  63.00   1.00    1.00    --   40.73 -57.00 120.00   59
  3  ω     49.00  92.00   1.00    1.00    --   40.73-125.00  30.00   43
  4  ω     72.00 107.00   1.00    1.00    --  107.58 -94.00 -60.00   35
  5  ω     82.00 120.00   1.00    1.00    --  107.58-125.00-120.00   38
  6  ω     46.00 136.00   1.00    1.00    --  107.58 -30.00   0.00   90
  7  ω     81.00 150.00   1.00    1.00    --  107.58  30.00 -60.00   69
  8  ω     93.00 128.00   1.00    1.00    --  107.58 -45.00 120.00   35
  9  ω     47.00 124.00   1.00    1.00    --  107.58 -30.00  90.00   77
 10  ω     40.00 119.00   1.00    1.00    --  107.58-125.00  90.00   79
 11  ω     39.00 134.00   1.00    1.00    --  107.58 -77.00  90.00   95
 12  ω     36.00 119.00   1.00    1.00    --  107.58 -61.00 -90.00   83
 13  ω     38.00  86.00   1.00    1.00    --  107.58 -77.00-120.00   48
 14  ω     28.00 153.00   1.00    1.00    --  107.58 -15.00 -90.00  125
 15  ω     24.00  79.00   1.00    1.00    --   40.73-125.00-150.00   55
 16  ω      9.00  48.00   1.00    1.00    --   40.73 -99.00 -90.00   39
 17  ω   -109.00 -18.00   1.00    1.00    --  -40.73 -38.00  30.00   91
 18  ω   -114.00 -21.00   1.00    1.00    --  -40.73 -38.00 -60.00   93
 19  ω    -32.00  -7.00   1.00    1.00    --  -40.73 125.00-180.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0777553000
_diffrn_orient_matrix_UB_12      0.0738851000
_diffrn_orient_matrix_UB_13      0.0036433000
_diffrn_orient_matrix_UB_21      0.0921704000
_diffrn_orient_matrix_UB_22      0.0914712000
_diffrn_orient_matrix_UB_23      0.0310483000
_diffrn_orient_matrix_UB_31      0.0161477000
_diffrn_orient_matrix_UB_32      -0.0032531000
_diffrn_orient_matrix_UB_33      -0.1052942000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                7877
_reflns_number_total             9628
_reflns_odcompleteness_completeness 99.99
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 Structure factors included contributions from the .fab file.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.073
_refine_diff_density_min         -0.732
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         9628
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1084
_refine_ls_R_factor_gt           0.0935
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0890P)²+14.3299P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2357
_refine_ls_wR_factor_ref         0.2462
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2. Others
 Sof(Cl7)=Sof(Cl8)=Sof(H25)=Sof(H26)=1-FVAR(1)
 Sof(Cl5)=Sof(Cl6)=Sof(H27)=Sof(H29)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C45(H45A,H45B)
3.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C5(H5), C6(H6A), N6(H6), C12(H12), C13(H13), C14(H14),
 C17(H17), C18(H18), C19(H19), C20(H20), N8(H8), C25(H25), C26(H26), C27(H27),
 C28(H28), C29(H29), N12(H12A), C35(H35), C36(H36), C37(H37), C40(H40),
 C41(H41), C42(H42), C43(H43)
3.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B), N5(H5A,H5B), N10(H10A,H10B), N11(H11A,H11B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.54690(11) 0.82676(11) 0.70993(12) 0.0407(4) Uani 1 1 d . . . . .
Cl2 Cl 0.56647(15) 0.93190(15) 0.92900(13) 0.0585(5) Uani 1 1 d . . . . .
N1 N 0.7956(4) 0.7173(4) 0.5987(3) 0.0312(10) Uani 1 1 d . . . . .
N2 N 0.8015(3) 0.6699(4) 0.5068(3) 0.0314(10) Uani 1 1 d . . . . .
H2 H 0.859714 0.685998 0.479101 0.038 Uiso 1 1 calc R . . . .
N3 N 0.6309(3) 0.5716(3) 0.4924(3) 0.0263(9) Uani 1 1 d . . . . .
N4 N 0.7387(3) 0.5555(4) 0.3657(3) 0.0304(10) Uani 1 1 d . . . . .
H4A H 0.799285 0.572978 0.342017 0.036 Uiso 1 1 calc R . . . .
H4B H 0.688579 0.508758 0.329866 0.036 Uiso 1 1 calc R . . . .
N5 N 0.5355(3) 0.5845(3) 0.6241(3) 0.0284(10) Uani 1 1 d . . . . .
H5A H 0.485495 0.536468 0.589624 0.034 Uiso 1 1 calc R . . . .
H5B H 0.527731 0.611975 0.684657 0.034 Uiso 1 1 calc R . . . .
C1 C 0.7103(4) 0.7388(4) 0.7430(4) 0.0287(11) Uani 1 1 d . . . . .
C2 C 0.6412(4) 0.8021(4) 0.7823(4) 0.0326(12) Uani 1 1 d . . . . .
C3 C 0.6510(5) 0.8508(5) 0.8808(4) 0.0388(14) Uani 1 1 d . . . . .
C4 C 0.7293(5) 0.8346(5) 0.9370(5) 0.0447(15) Uani 1 1 d . . . . .
H4 H 0.735934 0.867324 1.003387 0.054 Uiso 1 1 calc R . . . .
C5 C 0.7983(5) 0.7717(5) 0.8987(4) 0.0413(14) Uani 1 1 d . . . . .
H5 H 0.851851 0.762929 0.939931 0.050 Uiso 1 1 calc R . . . .
C6 C 0.7934(5) 0.7202(5) 0.8021(4) 0.0389(14) Uani 1 1 d . . . . .
H6A H 0.840901 0.675994 0.776653 0.047 Uiso 1 1 calc R . . . .
C7 C 0.7083(4) 0.6910(4) 0.6389(4) 0.0279(11) Uani 1 1 d . . . . .
C8 C 0.6228(4) 0.6156(4) 0.5846(4) 0.0253(10) Uani 1 1 d . . . . .
C9 C 0.7230(4) 0.5992(4) 0.4549(4) 0.0257(10) Uani 1 1 d . . . . .
Cl3 Cl 0.40620(11) 0.94400(12) 0.54415(12) 0.0449(4) Uani 1 1 d . . . . .
Cl4 Cl 0.03782(12) 0.80871(12) 0.68401(12) 0.0439(4) Uani 1 1 d . . . . .
O1 O -0.0713(3) 0.6445(3) 0.2989(3) 0.0327(9) Uani 1 1 d . . . . .
O2 O -0.0184(3) 0.7280(4) 0.4486(3) 0.0423(11) Uani 1 1 d . . . . .
N6 N 0.1842(3) 0.8215(3) 0.5286(3) 0.0285(9) Uani 1 1 d . . . . .
H6 H 0.125786 0.836009 0.507764 0.034 Uiso 1 1 calc R . . . .
C10 C 0.2261(4) 0.8740(4) 0.6201(4) 0.0261(10) Uani 1 1 d . . . . .
C11 C 0.3287(4) 0.9339(4) 0.6383(4) 0.0313(12) Uani 1 1 d . . . . .
C12 C 0.3686(5) 0.9894(5) 0.7287(5) 0.0419(15) Uani 1 1 d . . . . .
H12 H 0.438306 1.028106 0.737953 0.050 Uiso 1 1 calc R . . . .
C13 C 0.3088(6) 0.9890(5) 0.8049(5) 0.0465(16) Uani 1 1 d . . . . .
H13 H 0.336938 1.026803 0.867164 0.056 Uiso 1 1 calc R . . . .
C14 C 0.2053(6) 0.9325(5) 0.7912(4) 0.0428(15) Uani 1 1 d . . . . .
H14 H 0.162467 0.933249 0.843758 0.051 Uiso 1 1 calc R . . . .
C15 C 0.1665(4) 0.8756(4) 0.7001(4) 0.0312(12) Uani 1 1 d . . . . .
C16 C 0.2308(4) 0.7462(4) 0.4674(4) 0.0263(11) Uani 1 1 d . . . . .
C17 C 0.3143(4) 0.7090(4) 0.5006(4) 0.0315(12) Uani 1 1 d . . . . .
H17 H 0.339821 0.733471 0.565630 0.038 Uiso 1 1 calc R . . . .
C18 C 0.3597(5) 0.6360(5) 0.4381(4) 0.0383(13) Uani 1 1 d . . . . .
H18 H 0.417534 0.612046 0.460380 0.046 Uiso 1 1 calc R . . . .
C19 C 0.3218(5) 0.5979(5) 0.3440(4) 0.0407(14) Uani 1 1 d . . . . .
H19 H 0.352332 0.547000 0.302039 0.049 Uiso 1 1 calc R . . . .
C20 C 0.2388(4) 0.6344(5) 0.3113(4) 0.0341(12) Uani 1 1 d . . . . .
H20 H 0.212897 0.607885 0.246438 0.041 Uiso 1 1 calc R . . . .
C21 C 0.1925(4) 0.7088(4) 0.3709(4) 0.0279(11) Uani 1 1 d . . . . .
C22 C 0.1031(4) 0.7470(5) 0.3313(4) 0.0313(12) Uani 1 1 d . . . . .
H22A H 0.102790 0.728318 0.260842 0.038 Uiso 1 1 calc R . . . .
H22B H 0.115100 0.822402 0.354194 0.038 Uiso 1 1 calc R . . . .
C23 C -0.0039(4) 0.7032(5) 0.3603(4) 0.0311(12) Uani 1 1 d . . . . .
Cl5 Cl 0.89640(14) 0.82300(15) 0.16840(15) 0.0403(5) Uani 0.764(4) 1 d . . P A
1
Cl6 Cl 0.94778(17) 0.95439(16) 0.38038(17) 0.0524(7) Uani 0.764(4) 1 d . . P A
1
Cl7 Cl 0.6697(6) 0.8462(6) 0.4883(5) 0.0476(19) Uani 0.236(4) 1 d . . P A 2
Cl8 Cl 0.5688(5) 0.6897(5) 0.2996(5) 0.0384(16) Uani 0.236(4) 1 d . . P A 2
N7 N 0.6065(4) 0.7016(4) 0.0864(3) 0.0354(11) Uani 1 1 d . . . . .
N8 N 0.5705(4) 0.6419(4) -0.0004(3) 0.0329(10) Uani 1 1 d . . . . .
H8 H 0.517844 0.656802 -0.030169 0.039 Uiso 1 1 calc R . . . .
N9 N 0.6947(4) 0.5348(4) -0.0046(3) 0.0331(10) Uani 1 1 d . . . . .
N10 N 0.5677(4) 0.5039(4) -0.1278(4) 0.0408(12) Uani 1 1 d . . . . .
H10A H 0.592658 0.449698 -0.158018 0.049 Uiso 1 1 calc R . . . .
H10B H 0.513320 0.520671 -0.153361 0.049 Uiso 1 1 calc R . . . .
N11 N 0.8140(4) 0.5691(4) 0.1217(3) 0.0323(10) Uani 1 1 d . . . . .
H11A H 0.840021 0.514970 0.092830 0.039 Uiso 1 1 calc R . . . .
H11B H 0.841391 0.606844 0.178170 0.039 Uiso 1 1 calc R . . . .
C24 C 0.7174(6) 0.7456(5) 0.2265(4) 0.0452(16) Uani 1 1 d . . . . .
C25 C 0.8114(7) 0.8116(5) 0.2506(6) 0.060(2) Uani 1 1 d . . . . .
H25 H 0.862253 0.817129 0.204903 0.071 Uiso 0.236(4) 1 calc R . P A 2
C26 C 0.8313(7) 0.8739(6) 0.3501(7) 0.062(2) Uani 1 1 d . . . . .
H26 H 0.895318 0.921152 0.371737 0.074 Uiso 0.236(4) 1 calc R . P A 2
C27 C 0.7525(6) 0.8601(7) 0.4097(6) 0.0560(19) Uani 1 1 d . . . . .
H27 H 0.766349 0.899089 0.474234 0.067 Uiso 0.764(4) 1 calc R . P A 1
C28 C 0.6605(9) 0.7998(7) 0.3887(6) 0.073(3) Uani 1 1 d . . . . .
H28 H 0.610372 0.797920 0.435553 0.087 Uiso 1 1 calc R . . . .
C29 C 0.6380(9) 0.7388(7) 0.2966(5) 0.067(3) Uani 1 1 d . . . . .
H29 H 0.572240 0.693261 0.278958 0.080 Uiso 0.764(4) 1 calc R . P A 1
C30 C 0.6872(4) 0.6808(4) 0.1281(4) 0.0304(11) Uani 1 1 d . . . . .
C31 C 0.7339(4) 0.5935(4) 0.0804(4) 0.0271(11) Uani 1 1 d . . . . .
C32 C 0.6120(4) 0.5605(4) -0.0435(4) 0.0298(11) Uani 1 1 d . . . . .
Cl9 Cl 0.40455(11) 0.79072(12) 0.16504(11) 0.0426(4) Uani 1 1 d . . . . .
Cl10 Cl 0.07869(12) 0.92251(13) 0.02463(11) 0.0439(4) Uani 1 1 d . . . . .
O3 O 0.4111(3) 0.5892(3) -0.2155(3) 0.0317(8) Uani 1 1 d . . . . .
O4 O 0.4131(3) 0.6952(4) -0.0706(3) 0.0447(11) Uani 1 1 d . . . . .
N12 N 0.2516(4) 0.7939(4) 0.0114(3) 0.0309(10) Uani 1 1 d . . . . .
H12A H 0.314759 0.803282 -0.010479 0.037 Uiso 1 1 calc R . . . .
C33 C 0.2366(4) 0.8545(4) 0.1019(4) 0.0304(11) Uani 1 1 d . . . . .
C34 C 0.3035(4) 0.8612(5) 0.1813(4) 0.0331(12) Uani 1 1 d . . . . .
C35 C 0.2966(5) 0.9247(5) 0.2699(5) 0.0443(15) Uani 1 1 d . . . . .
H35 H 0.343777 0.926790 0.321561 0.053 Uiso 1 1 calc R . . . .
C36 C 0.2201(5) 0.9861(5) 0.2838(4) 0.0445(16) Uani 1 1 d . . . . .
H36 H 0.214622 1.030173 0.344956 0.053 Uiso 1 1 calc R . . . .
C37 C 0.1517(5) 0.9822(5) 0.2072(4) 0.0399(14) Uani 1 1 d . . . . .
H37 H 0.099151 1.023721 0.215834 0.048 Uiso 1 1 calc R . . . .
C38 C 0.1607(5) 0.9172(4) 0.1180(4) 0.0340(12) Uani 1 1 d . . . . .
C39 C 0.1715(4) 0.7185(4) -0.0472(4) 0.0280(11) Uani 1 1 d . . . . .
C40 C 0.0771(4) 0.6834(5) -0.0095(4) 0.0343(12) Uani 1 1 d . . . . .
H40 H 0.067456 0.708504 0.056459 0.041 Uiso 1 1 calc R . . . .
C41 C -0.0023(5) 0.6119(5) -0.0684(5) 0.0377(13) Uani 1 1 d . . . . .
H41 H -0.065986 0.587830 -0.042779 0.045 Uiso 1 1 calc R . . . .
C42 C 0.0119(5) 0.5759(4) -0.1645(5) 0.0379(14) Uani 1 1 d . . . . .
H42 H -0.042778 0.528609 -0.205491 0.045 Uiso 1 1 calc R . . . .
C43 C 0.1061(4) 0.6091(4) -0.2004(4) 0.0332(12) Uani 1 1 d . . . . .
H43 H 0.115490 0.583392 -0.266334 0.040 Uiso 1 1 calc R . . . .
C44 C 0.1877(4) 0.6794(4) -0.1427(4) 0.0283(11) Uani 1 1 d . . . . .
C45 C 0.2906(4) 0.7089(4) -0.1870(4) 0.0305(11) Uani 1 1 d . . . . .
H45A H 0.312523 0.784086 -0.167424 0.037 Uiso 1 1 calc R . . . .
H45B H 0.278720 0.687029 -0.257326 0.037 Uiso 1 1 calc R . . . .
C46 C 0.3787(4) 0.6604(4) -0.1573(4) 0.0288(11) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.728(6) . ?
Cl2 C3 1.724(7) . ?
N1 N2 1.338(6) . ?
N1 C7 1.315(7) . ?
N2 H2 0.8800 . ?
N2 C9 1.339(7) . ?
N3 C8 1.335(7) . ?
N3 C9 1.351(6) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C9 1.316(7) . ?
N5 H5A 0.8800 . ?
N5 H5B 0.8800 . ?
N5 C8 1.328(7) . ?
C1 C2 1.382(8) . ?
C1 C6 1.461(8) . ?
C1 C7 1.484(8) . ?
C2 C3 1.410(8) . ?
C3 C4 1.372(9) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(9) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(8) . ?
C6 H6A 0.9500 . ?
C7 C8 1.438(7) . ?
Cl3 C11 1.731(6) . ?
Cl4 C15 1.732(6) . ?
O1 C23 1.250(7) . ?
O2 C23 1.266(7) . ?
N6 H6 0.8800 . ?
N6 C10 1.388(7) . ?
N6 C16 1.409(7) . ?
C10 C11 1.413(7) . ?
C10 C15 1.404(8) . ?
C11 C12 1.377(8) . ?
C12 H12 0.9500 . ?
C12 C13 1.363(10) . ?
C13 H13 0.9500 . ?
C13 C14 1.405(10) . ?
C14 H14 0.9500 . ?
C14 C15 1.388(8) . ?
C16 C17 1.399(8) . ?
C16 C21 1.413(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.390(8) . ?
C18 H18 0.9500 . ?
C18 C19 1.380(9) . ?
C19 H19 0.9500 . ?
C19 C20 1.385(9) . ?
C20 H20 0.9500 . ?
C20 C21 1.389(8) . ?
C21 C22 1.510(7) . ?
C22 H22A 0.9900 . ?
C22 H22B 0.9900 . ?
C22 C23 1.520(7) . ?
Cl5 C25 1.656(10) . ?
Cl6 C26 1.681(9) . ?
Cl7 C27 1.603(11) . ?
Cl8 C29 1.031(12) . ?
N7 N8 1.340(6) . ?
N7 C30 1.306(7) . ?
N8 H8 0.8800 . ?
N8 C32 1.340(7) . ?
N9 C31 1.326(7) . ?
N9 C32 1.340(7) . ?
N10 H10A 0.8800 . ?
N10 H10B 0.8800 . ?
N10 C32 1.328(7) . ?
N11 H11A 0.8800 . ?
N11 H11B 0.8800 . ?
N11 C31 1.322(7) . ?
C24 C25 1.363(11) . ?
C24 C29 1.466(12) . ?
C24 C30 1.482(8) . ?
C25 H25 0.9500 . ?
C25 C26 1.472(11) . ?
C26 H26 0.9500 . ?
C26 C27 1.367(12) . ?
C27 H27 0.9500 . ?
C27 C28 1.305(13) . ?
C28 H28 0.9500 . ?
C28 C29 1.380(11) . ?
C29 H29 0.9500 . ?
C30 C31 1.458(7) . ?
Cl9 C34 1.740(6) . ?
Cl10 C38 1.731(6) . ?
O3 C46 1.256(7) . ?
O4 C46 1.270(7) . ?
N12 H12A 0.8800 . ?
N12 C33 1.401(7) . ?
N12 C39 1.418(7) . ?
C33 C34 1.403(8) . ?
C33 C38 1.399(8) . ?
C34 C35 1.373(9) . ?
C35 H35 0.9500 . ?
C35 C36 1.390(10) . ?
C36 H36 0.9500 . ?
C36 C37 1.394(10) . ?
C37 H37 0.9500 . ?
C37 C38 1.393(8) . ?
C39 C40 1.405(8) . ?
C39 C44 1.388(8) . ?
C40 H40 0.9500 . ?
C40 C41 1.391(8) . ?
C41 H41 0.9500 . ?
C41 C42 1.384(9) . ?
C42 H42 0.9500 . ?
C42 C43 1.383(9) . ?
C43 H43 0.9500 . ?
C43 C44 1.395(8) . ?
C44 C45 1.522(7) . ?
C45 H45A 0.9900 . ?
C45 H45B 0.9900 . ?
C45 C46 1.524(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 N2 117.3(4) . . ?
N1 N2 H2 118.4 . . ?
N1 N2 C9 123.2(4) . . ?
C9 N2 H2 118.4 . . ?
C8 N3 C9 117.0(4) . . ?
H4A N4 H4B 120.0 . . ?
C9 N4 H4A 120.0 . . ?
C9 N4 H4B 120.0 . . ?
H5A N5 H5B 120.0 . . ?
C8 N5 H5A 120.0 . . ?
C8 N5 H5B 120.0 . . ?
C2 C1 C6 121.1(5) . . ?
C2 C1 C7 122.4(5) . . ?
C6 C1 C7 116.5(5) . . ?
C1 C2 Cl1 120.1(4) . . ?
C1 C2 C3 120.0(5) . . ?
C3 C2 Cl1 119.9(5) . . ?
C2 C3 Cl2 119.8(5) . . ?
C4 C3 Cl2 120.7(5) . . ?
C4 C3 C2 119.5(6) . . ?
C3 C4 H4 119.5 . . ?
C3 C4 C5 121.0(6) . . ?
C5 C4 H4 119.5 . . ?
C4 C5 H5 118.5 . . ?
C4 C5 C6 123.1(6) . . ?
C6 C5 H5 118.5 . . ?
C1 C6 H6A 122.3 . . ?
C5 C6 C1 115.4(6) . . ?
C5 C6 H6A 122.3 . . ?
N1 C7 C1 114.8(5) . . ?
N1 C7 C8 120.5(5) . . ?
C8 C7 C1 124.5(5) . . ?
N3 C8 C7 120.3(5) . . ?
N5 C8 N3 117.8(5) . . ?
N5 C8 C7 121.9(5) . . ?
N2 C9 N3 121.6(5) . . ?
N4 C9 N2 118.0(5) . . ?
N4 C9 N3 120.4(5) . . ?
C10 N6 H6 118.4 . . ?
C10 N6 C16 123.2(4) . . ?
C16 N6 H6 118.4 . . ?
N6 C10 C11 122.5(5) . . ?
N6 C10 C15 121.8(5) . . ?
C15 C10 C11 115.6(5) . . ?
C10 C11 Cl3 119.6(4) . . ?
C12 C11 Cl3 117.8(5) . . ?
C12 C11 C10 122.5(5) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(6) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(6) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.2(6) . . ?
C15 C14 H14 120.4 . . ?
C10 C15 Cl4 118.9(4) . . ?
C14 C15 Cl4 118.7(5) . . ?
C14 C15 C10 122.4(5) . . ?
N6 C16 C21 119.0(5) . . ?
C17 C16 N6 121.1(5) . . ?
C17 C16 C21 119.9(5) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 C16 119.7(5) . . ?
C18 C17 H17 120.1 . . ?
C17 C18 H18 119.6 . . ?
C19 C18 C17 120.8(5) . . ?
C19 C18 H18 119.6 . . ?
C18 C19 H19 120.3 . . ?
C18 C19 C20 119.5(5) . . ?
C20 C19 H19 120.3 . . ?
C19 C20 H20 119.2 . . ?
C19 C20 C21 121.6(5) . . ?
C21 C20 H20 119.2 . . ?
C16 C21 C22 122.0(5) . . ?
C20 C21 C16 118.5(5) . . ?
C20 C21 C22 119.5(5) . . ?
C21 C22 H22A 109.1 . . ?
C21 C22 H22B 109.1 . . ?
C21 C22 C23 112.5(4) . . ?
H22A C22 H22B 107.8 . . ?
C23 C22 H22A 109.1 . . ?
C23 C22 H22B 109.1 . . ?
O1 C23 O2 123.4(5) . . ?
O1 C23 C22 120.3(5) . . ?
O2 C23 C22 116.3(5) . . ?
C30 N7 N8 118.1(5) . . ?
N7 N8 H8 118.9 . . ?
N7 N8 C32 122.3(5) . . ?
C32 N8 H8 118.9 . . ?
C31 N9 C32 116.7(5) . . ?
H10A N10 H10B 120.0 . . ?
C32 N10 H10A 120.0 . . ?
C32 N10 H10B 120.0 . . ?
H11A N11 H11B 120.0 . . ?
C31 N11 H11A 120.0 . . ?
C31 N11 H11B 120.0 . . ?
C25 C24 C29 121.2(7) . . ?
C25 C24 C30 122.5(7) . . ?
C29 C24 C30 116.2(7) . . ?
C24 C25 Cl5 120.1(6) . . ?
C24 C25 H25 121.2 . . ?
C24 C25 C26 117.6(8) . . ?
C26 C25 Cl5 122.3(7) . . ?
C26 C25 H25 121.2 . . ?
C25 C26 Cl6 117.7(7) . . ?
C25 C26 H26 121.9 . . ?
C27 C26 Cl6 126.1(7) . . ?
C27 C26 C25 116.3(8) . . ?
C27 C26 H26 121.9 . . ?
C26 C27 Cl7 173.9(7) . . ?
C26 C27 H27 116.0 . . ?
C28 C27 Cl7 57.3(6) . . ?
C28 C27 C26 127.9(9) . . ?
C28 C27 H27 116.0 . . ?
C27 C28 H28 120.9 . . ?
C27 C28 C29 118.3(10) . . ?
C29 C28 H28 120.9 . . ?
Cl8 C29 C24 135.8(8) . . ?
Cl8 C29 C28 104.6(9) . . ?
C24 C29 H29 120.6 . . ?
C28 C29 C24 118.8(10) . . ?
C28 C29 H29 120.6 . . ?
N7 C30 C24 114.8(5) . . ?
N7 C30 C31 119.6(5) . . ?
C31 C30 C24 125.4(5) . . ?
N9 C31 C30 120.6(5) . . ?
N11 C31 N9 118.3(5) . . ?
N11 C31 C30 121.1(5) . . ?
N9 C32 N8 122.6(5) . . ?
N10 C32 N8 117.5(5) . . ?
N10 C32 N9 119.9(5) . . ?
C33 N12 H12A 117.9 . . ?
C33 N12 C39 124.2(5) . . ?
C39 N12 H12A 117.9 . . ?
N12 C33 C34 121.0(5) . . ?
C38 C33 N12 123.0(5) . . ?
C38 C33 C34 115.8(5) . . ?
C33 C34 Cl9 118.3(4) . . ?
C35 C34 Cl9 118.4(5) . . ?
C35 C34 C33 123.2(6) . . ?
C34 C35 H35 120.1 . . ?
C34 C35 C36 119.7(6) . . ?
C36 C35 H35 120.1 . . ?
C35 C36 H36 120.3 . . ?
C35 C36 C37 119.3(6) . . ?
C37 C36 H36 120.3 . . ?
C36 C37 H37 120.1 . . ?
C38 C37 C36 119.7(6) . . ?
C38 C37 H37 120.1 . . ?
C33 C38 Cl10 120.6(4) . . ?
C37 C38 Cl10 117.1(5) . . ?
C37 C38 C33 122.2(6) . . ?
C40 C39 N12 120.8(5) . . ?
C44 C39 N12 119.0(5) . . ?
C44 C39 C40 120.2(5) . . ?
C39 C40 H40 119.9 . . ?
C41 C40 C39 120.2(5) . . ?
C41 C40 H40 119.9 . . ?
C40 C41 H41 120.2 . . ?
C42 C41 C40 119.7(6) . . ?
C42 C41 H41 120.2 . . ?
C41 C42 H42 120.2 . . ?
C43 C42 C41 119.7(5) . . ?
C43 C42 H42 120.2 . . ?
C42 C43 H43 119.1 . . ?
C42 C43 C44 121.8(6) . . ?
C44 C43 H43 119.1 . . ?
C39 C44 C43 118.3(5) . . ?
C39 C44 C45 123.1(5) . . ?
C43 C44 C45 118.5(5) . . ?
C44 C45 H45A 109.2 . . ?
C44 C45 H45B 109.2 . . ?
C44 C45 C46 112.1(5) . . ?
H45A C45 H45B 107.9 . . ?
C46 C45 H45A 109.2 . . ?
C46 C45 H45B 109.2 . . ?
O3 C46 O4 123.9(5) . . ?
O3 C46 C45 120.9(5) . . ?
O4 C46 C45 115.2(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C2 C3 Cl2 1.8(7) . . . . ?
Cl1 C2 C3 C4 -176.9(5) . . . . ?
Cl2 C3 C4 C5 -178.6(5) . . . . ?
N1 N2 C9 N3 0.8(9) . . . . ?
N1 N2 C9 N4 -178.1(5) . . . . ?
N1 C7 C8 N3 -0.3(8) . . . . ?
N1 C7 C8 N5 177.2(5) . . . . ?
N2 N1 C7 C1 174.5(5) . . . . ?
N2 N1 C7 C8 -1.1(8) . . . . ?
C1 C2 C3 Cl2 178.5(4) . . . . ?
C1 C2 C3 C4 -0.2(9) . . . . ?
C1 C7 C8 N3 -175.4(5) . . . . ?
C1 C7 C8 N5 2.1(8) . . . . ?
C2 C1 C6 C5 -1.2(8) . . . . ?
C2 C1 C7 N1 118.6(6) . . . . ?
C2 C1 C7 C8 -66.0(8) . . . . ?
C2 C3 C4 C5 0.1(10) . . . . ?
C3 C4 C5 C6 -0.5(11) . . . . ?
C4 C5 C6 C1 1.1(9) . . . . ?
C6 C1 C2 Cl1 177.5(4) . . . . ?
C6 C1 C2 C3 0.8(8) . . . . ?
C6 C1 C7 N1 -58.2(7) . . . . ?
C6 C1 C7 C8 117.2(6) . . . . ?
C7 N1 N2 C9 0.9(8) . . . . ?
C7 C1 C2 Cl1 0.8(7) . . . . ?
C7 C1 C2 C3 -175.9(5) . . . . ?
C7 C1 C6 C5 175.7(5) . . . . ?
C8 N3 C9 N2 -2.1(8) . . . . ?
C8 N3 C9 N4 176.7(5) . . . . ?
C9 N3 C8 N5 -175.7(5) . . . . ?
C9 N3 C8 C7 1.8(7) . . . . ?
Cl3 C11 C12 C13 176.3(5) . . . . ?
N6 C10 C11 Cl3 0.4(7) . . . . ?
N6 C10 C11 C12 177.3(5) . . . . ?
N6 C10 C15 Cl4 0.9(7) . . . . ?
N6 C10 C15 C14 -176.2(5) . . . . ?
N6 C16 C17 C18 -178.9(5) . . . . ?
N6 C16 C21 C20 -179.9(5) . . . . ?
N6 C16 C21 C22 -0.1(7) . . . . ?
C10 N6 C16 C17 9.5(8) . . . . ?
C10 N6 C16 C21 -169.9(5) . . . . ?
C10 C11 C12 C13 -0.6(10) . . . . ?
C11 C10 C15 Cl4 177.4(4) . . . . ?
C11 C10 C15 C14 0.3(8) . . . . ?
C11 C12 C13 C14 -0.6(10) . . . . ?
C12 C13 C14 C15 1.6(10) . . . . ?
C13 C14 C15 Cl4 -178.6(5) . . . . ?
C13 C14 C15 C10 -1.5(9) . . . . ?
C15 C10 C11 Cl3 -176.0(4) . . . . ?
C15 C10 C11 C12 0.8(8) . . . . ?
C16 N6 C10 C11 59.4(7) . . . . ?
C16 N6 C10 C15 -124.3(6) . . . . ?
C16 C17 C18 C19 -1.6(9) . . . . ?
C16 C21 C22 C23 -76.0(7) . . . . ?
C17 C16 C21 C20 0.7(8) . . . . ?
C17 C16 C21 C22 -179.6(5) . . . . ?
C17 C18 C19 C20 1.3(10) . . . . ?
C18 C19 C20 C21 0.1(10) . . . . ?
C19 C20 C21 C16 -1.0(9) . . . . ?
C19 C20 C21 C22 179.2(5) . . . . ?
C20 C21 C22 C23 103.7(6) . . . . ?
C21 C16 C17 C18 0.6(8) . . . . ?
C21 C22 C23 O1 -114.2(6) . . . . ?
C21 C22 C23 O2 64.5(7) . . . . ?
Cl5 C25 C26 Cl6 -3.3(8) . . . . ?
Cl5 C25 C26 C27 177.1(5) . . . . ?
Cl6 C26 C27 C28 178.8(7) . . . . ?
Cl7 C27 C28 C29 -173.9(10) . . . . ?
N7 N8 C32 N9 -2.5(9) . . . . ?
N7 N8 C32 N10 177.2(5) . . . . ?
N7 C30 C31 N9 -0.4(8) . . . . ?
N7 C30 C31 N11 -178.4(5) . . . . ?
N8 N7 C30 C24 -175.9(5) . . . . ?
N8 N7 C30 C31 -1.1(8) . . . . ?
C24 C25 C26 Cl6 179.3(5) . . . . ?
C24 C25 C26 C27 -0.3(9) . . . . ?
C24 C30 C31 N9 173.8(6) . . . . ?
C24 C30 C31 N11 -4.1(9) . . . . ?
C25 C24 C29 Cl8 -168.4(10) . . . . ?
C25 C24 C29 C28 -0.9(10) . . . . ?
C25 C24 C30 N7 -114.8(7) . . . . ?
C25 C24 C30 C31 70.7(9) . . . . ?
C25 C26 C27 C28 -1.6(12) . . . . ?
C26 C27 C28 C29 2.2(13) . . . . ?
C27 C28 C29 Cl8 170.1(9) . . . . ?
C27 C28 C29 C24 -0.9(11) . . . . ?
C29 C24 C25 Cl5 -176.1(5) . . . . ?
C29 C24 C25 C26 1.4(9) . . . . ?
C29 C24 C30 N7 62.4(8) . . . . ?
C29 C24 C30 C31 -112.1(7) . . . . ?
C30 N7 N8 C32 2.5(8) . . . . ?
C30 C24 C25 Cl5 0.9(9) . . . . ?
C30 C24 C25 C26 178.4(6) . . . . ?
C30 C24 C29 Cl8 14.4(14) . . . . ?
C30 C24 C29 C28 -178.0(6) . . . . ?
C31 N9 C32 N8 0.9(8) . . . . ?
C31 N9 C32 N10 -178.8(5) . . . . ?
C32 N9 C31 N11 178.5(5) . . . . ?
C32 N9 C31 C30 0.5(8) . . . . ?
Cl9 C34 C35 C36 176.6(5) . . . . ?
N12 C33 C34 Cl9 -1.0(8) . . . . ?
N12 C33 C34 C35 175.4(6) . . . . ?
N12 C33 C38 Cl10 0.5(8) . . . . ?
N12 C33 C38 C37 -175.5(5) . . . . ?
N12 C39 C40 C41 177.9(5) . . . . ?
N12 C39 C44 C43 -176.8(5) . . . . ?
N12 C39 C44 C45 3.7(8) . . . . ?
C33 N12 C39 C40 -14.5(8) . . . . ?
C33 N12 C39 C44 165.8(5) . . . . ?
C33 C34 C35 C36 0.2(9) . . . . ?
C34 C33 C38 Cl10 175.9(4) . . . . ?
C34 C33 C38 C37 -0.1(8) . . . . ?
C34 C35 C36 C37 -0.2(9) . . . . ?
C35 C36 C37 C38 0.0(9) . . . . ?
C36 C37 C38 Cl10 -175.9(5) . . . . ?
C36 C37 C38 C33 0.1(9) . . . . ?
C38 C33 C34 Cl9 -176.4(4) . . . . ?
C38 C33 C34 C35 -0.1(9) . . . . ?
C39 N12 C33 C34 127.4(6) . . . . ?
C39 N12 C33 C38 -57.5(8) . . . . ?
C39 C40 C41 C42 -0.3(9) . . . . ?
C39 C44 C45 C46 73.7(7) . . . . ?
C40 C39 C44 C43 3.5(8) . . . . ?
C40 C39 C44 C45 -176.1(5) . . . . ?
C40 C41 C42 C43 1.9(9) . . . . ?
C41 C42 C43 C44 -0.8(9) . . . . ?
C42 C43 C44 C39 -1.9(8) . . . . ?
C42 C43 C44 C45 177.6(5) . . . . ?
C43 C44 C45 C46 -105.8(6) . . . . ?
C44 C39 C40 C41 -2.4(8) . . . . ?
C44 C45 C46 O3 108.2(6) . . . . ?
C44 C45 C46 O4 -69.8(7) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.500 95.6 25.3 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.575
_oxdiff_exptl_absorpt_empirical_full_min 0.635
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_04-1222
_database_code_depnum_ccdc_archive 'CCDC 2380264'
loop_
_audit_author_name
_audit_author_address
'Zhengzheng Zhou'
;Southern Medical University
China
;
_audit_update_record             
;
2024-08-28 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_date             2024-08-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_formula_moiety         'C9 H8 Cl2 N5, C15 H14 N O2, C2 H6 O'
_chemical_formula_sum            'C26 H28 Cl2 N6 O3'
_chemical_formula_weight         543.46
_chemical_oxdiff_formula         'C24 H24 N24 O24 Cl0 '
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.01920 0.00962 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
Cl 0.36843 0.69943 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55739974976
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.05239 0.03377 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.03256 0.01839 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   8.9451(9)
_cell_length_b                   10.4421(9)
_cell_length_c                   15.1087(13)
_cell_angle_alpha                75.104(7)
_cell_angle_beta                 73.770(8)
_cell_angle_gamma                75.903(8)
_cell_volume                     1286.8(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3171
_cell_measurement_temperature    150.00(10)
_cell_measurement_theta_max      73.8170
_cell_measurement_theta_min      3.0890
_exptl_absorpt_coefficient_mu    2.609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45651
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.4024
_exptl_crystal_description       block
_exptl_crystal_F_000             571.0789
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_unetI/netI     0.0662
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9020
_diffrn_reflns_theta_full        74.3521
_diffrn_reflns_theta_max         74.35
_diffrn_reflns_theta_min         3.11
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      150.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9610
_diffrn_measured_fraction_theta_max 0.9610
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -56.00  33.00   1.00    1.00    --  -41.42  38.00-150.00   89
  2  ω     33.00  83.00   1.00    1.00    --   41.42-125.00 -60.00   50
  3  ω     34.00 133.00   1.00    2.00    --  107.51 -45.00-150.00   99
  4  ω     79.00 153.00   1.00    2.00    --  107.51  15.00-180.00   74
  5  ω    110.00 163.00   1.00    2.00    --  107.51 125.00 -30.00   53
  6  ω     85.00 157.00   1.00    2.00    --  107.51  30.00  30.00   72
  7  ω     82.00 121.00   1.00    2.00    --  107.51  61.00  60.00   39
  8  ω     79.00 172.00   1.00    2.00    --  107.51  30.00 -90.00   93
  9  ω     73.00 101.00   1.00    2.00    --  107.51 -94.00-180.00   28
 10  ω     70.00 131.00   1.00    2.00    --  107.51 -61.00 -60.00   61
 11  ω     70.00 115.00   1.00    2.00    --  107.51-125.00 -60.00   45
 12  ω     43.00 105.00   1.00    2.00    --  107.51 -94.00 -30.00   62
 13  ω     35.00 134.00   1.00    2.00    --  107.51 -61.00  60.00   99
 14  ω     78.00 119.00   1.00    2.00    --  107.51-125.00 120.00   41
 15  ω    -91.00  -3.00   1.00    1.00    --  -41.42 125.00  30.00   88
 16  ω   -106.00 -42.00   1.00    1.00    --  -41.42 -38.00   0.00   64
 17  ω   -114.00 -14.00   1.00    1.00    --  -41.42 -57.00 -90.00  100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1053139000
_diffrn_orient_matrix_UB_12      -0.1261310000
_diffrn_orient_matrix_UB_13      -0.0348139000
_diffrn_orient_matrix_UB_21      -0.0257468000
_diffrn_orient_matrix_UB_22      0.0625505000
_diffrn_orient_matrix_UB_23      -0.0999313000
_diffrn_orient_matrix_UB_31      0.1468500000
_diffrn_orient_matrix_UB_32      0.0656776000
_diffrn_orient_matrix_UB_33      -0.0237494000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -12
_reflns_limit_l_max              18
_reflns_limit_l_min              0
_reflns_number_gt                3896
_reflns_number_total             5026
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.9781
_refine_diff_density_min         -0.7712
_refine_diff_density_rms         0.1712
_refine_ls_d_res_high            0.8006
_refine_ls_d_res_low             14.2047
_refine_ls_goodness_of_fit_ref   1.0663
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    47
_refine_ls_number_parameters     338
_refine_ls_number_reflns         5026
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0956
_refine_ls_R_factor_gt           0.0745
_refine_ls_restrained_S_all      1.0663
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1402P)²+0.9572P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2117
_refine_ls_wR_factor_ref         0.2345
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C25(H25a,H25b)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C4(H4), C5(H5), C6(H6a), N6(H6), C11(H11), C12(H12), C13(H13),
 C20(H20), C19(H19), C18(H18), C17(H17)
2.c X=CH2 refined with riding coordinates:
 N5(H5a,H5b), N4(H4a,H4b)
2.d Idealised Me refined as rotating group:
 C24(H24a,H24b,H24c), C23(H23a,H23b,H23c), C26(H26a,H26b,H26c)
2.e Idealised tetrahedral OH refined as rotating group:
 O3(H3)
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
Cl1 Cl 0.76042(11) 0.71207(9) 0.21870(6) 0.0320(3) Uani 1.000000 .
Cl2 Cl 0.81987(15) 0.94165(11) 0.04013(7) 0.0471(3) Uani 1.000000 .
N5 N 0.5451(4) 0.5039(3) 0.6130(2) 0.0291(7) Uani 1.000000 .
H5a H 0.6028(4) 0.4289(3) 0.6371(2) 0.0350(8) Uiso 1.000000 R
H5b H 0.4415(4) 0.5189(3) 0.6339(2) 0.0350(8) Uiso 1.000000 R
N1 N 0.7722(3) 0.5733(3) 0.5122(2) 0.0240(6) Uani 1.000000 .
N2 N 0.5183(3) 0.7071(3) 0.5106(2) 0.0243(6) Uani 1.000000 .
H2 H 0.4163(3) 0.7194(3) 0.5370(2) 0.0291(7) Uiso 1.000000 R
N3 N 0.5752(3) 0.8009(3) 0.4367(2) 0.0250(6) Uani 1.000000 .
N4 N 0.9860(3) 0.6527(3) 0.4070(2) 0.0280(6) Uani 1.000000 .
H4a H 1.0496(3) 0.5814(3) 0.4305(2) 0.0336(8) Uiso 1.000000 R
H4b H 1.0255(3) 0.7145(3) 0.3604(2) 0.0336(8) Uiso 1.000000 R
C9 C 0.6146(4) 0.5947(3) 0.5448(2) 0.0241(7) Uani 1.000000 .
C8 C 0.8314(4) 0.6671(3) 0.4417(2) 0.0239(7) Uani 1.000000 .
C7 C 0.7256(4) 0.7843(3) 0.4023(2) 0.0237(7) Uani 1.000000 .
C1 C 0.7800(4) 0.8868(4) 0.3177(2) 0.0245(7) Uani 1.000000 .
C2 C 0.7906(4) 0.8644(3) 0.2281(3) 0.0260(7) Uani 1.000000 .
C3 C 0.8215(5) 0.9648(4) 0.1492(2) 0.0296(8) Uani 1.000000 .
C4 C 0.8490(5) 1.0864(4) 0.1572(3) 0.0321(8) Uani 1.000000 .
H4 H 0.8726(5) 1.1543(4) 0.1026(3) 0.0385(9) Uiso 1.000000 R
C5 C 0.8420(5) 1.1080(4) 0.2448(3) 0.0305(8) Uani 1.000000 .
H5 H 0.8616(5) 1.1908(4) 0.2502(3) 0.0366(9) Uiso 1.000000 R
C6 C 0.8062(4) 1.0094(4) 0.3250(3) 0.0271(7) Uani 1.000000 .
H6a H 0.7997(4) 1.0257(4) 0.3852(3) 0.0325(9) Uiso 1.000000 R
O1 O -0.2055(3) 0.4063(3) 0.34456(19) 0.0315(6) Uani 1.000000 .
O2 O -0.2132(3) 0.2340(3) 0.46655(18) 0.0290(6) Uani 1.000000 .
N6 N 0.0742(4) 0.4458(4) 0.2314(2) 0.0353(8) Uani 1.000000 .
H6 H -0.0289(4) 0.4744(4) 0.2455(2) 0.0424(9) Uiso 1.000000 R
C10 C 0.1652(4) 0.5176(4) 0.1489(3) 0.0288(7) Uani 1.000000 .
C11 C 0.2169(5) 0.6303(4) 0.1544(3) 0.0354(8) Uani 1.000000 .
H11 H 0.1915(5) 0.6577(4) 0.2129(3) 0.0425(10) Uiso 1.000000 R
C12 C 0.3045(6) 0.7021(4) 0.0758(3) 0.0393(9) Uani 1.000000 .
H12 H 0.3409(6) 0.7779(4) 0.0803(3) 0.0471(11) Uiso 1.000000 R
C13 C 0.3392(5) 0.6634(4) -0.0098(3) 0.0328(8) Uani 1.000000 .
H13 H 0.3991(5) 0.7134(4) -0.0641(3) 0.0394(10) Uiso 1.000000 R
C14 C 0.2876(4) 0.5526(4) -0.0173(3) 0.0294(7) Uani 1.000000 .
C15 C 0.2009(4) 0.4769(4) 0.0628(3) 0.0281(7) Uani 1.000000 .
C24 C 0.3230(6) 0.5162(5) -0.1130(3) 0.0456(11) Uani 1.000000 .
H24a H 0.2233(6) 0.519(4) -0.1290(13) 0.0684(16) Uiso 1.000000 GR
H24b H 0.381(4) 0.581(2) -0.1606(5) 0.0684(16) Uiso 1.000000 GR
H24c H 0.387(4) 0.4253(16) -0.1111(8) 0.0684(16) Uiso 1.000000 GR
C23 C 0.1505(6) 0.3534(5) 0.0556(3) 0.0449(10) Uani 1.000000 .
H23a H 0.080(4) 0.3790(7) 0.012(2) 0.0673(15) Uiso 1.000000 GR
H23b H 0.2443(7) 0.2891(17) 0.032(3) 0.0673(15) Uiso 1.000000 GR
H23c H 0.094(4) 0.312(2) 0.1179(6) 0.0673(15) Uiso 1.000000 GR
C16 C 0.1368(4) 0.3358(3) 0.2897(2) 0.0252(7) Uani 1.000000 .
C21 C 0.0406(4) 0.2652(3) 0.3694(2) 0.0233(7) Uani 1.000000 .
C22 C -0.1379(4) 0.3074(3) 0.3946(2) 0.0230(7) Uani 1.000000 .
C20 C 0.1111(4) 0.1520(4) 0.4256(2) 0.0259(7) Uani 1.000000 .
H20 H 0.0458(4) 0.1047(4) 0.4786(2) 0.0311(8) Uiso 1.000000 R
C19 C 0.2733(4) 0.1060(4) 0.4068(3) 0.0276(7) Uani 1.000000 .
H19 H 0.3190(4) 0.0289(4) 0.4464(3) 0.0332(9) Uiso 1.000000 R
C18 C 0.3685(4) 0.1759(4) 0.3281(3) 0.0311(8) Uani 1.000000 .
H18 H 0.4800(4) 0.1456(4) 0.3140(3) 0.0374(9) Uiso 1.000000 R
C17 C 0.3027(4) 0.2872(4) 0.2713(3) 0.0303(8) Uani 1.000000 .
H17 H 0.3697(4) 0.3330(4) 0.2184(3) 0.0364(9) Uiso 1.000000 R
O3 O 0.2599(3) 0.7692(3) 0.33991(19) 0.0348(6) Uani 1.000000 .
H3 H 0.238(6) 0.798(3) 0.3901(9) 0.0522(9) Uiso 1.000000 GR
C25 C 0.3489(5) 0.8569(4) 0.2654(3) 0.0326(8) Uani 1.000000 .
H25a H 0.4140(5) 0.8947(4) 0.2920(3) 0.0391(9) Uiso 1.000000 R
H25b H 0.4217(5) 0.8038(4) 0.2196(3) 0.0391(9) Uiso 1.000000 R
C26 C 0.2445(6) 0.9703(4) 0.2152(3) 0.0421(10) Uani 1.000000 .
H26a H 0.3099(6) 1.020(2) 0.1601(15) 0.0631(15) Uiso 1.000000 GR
H26b H 0.171(3) 0.9338(5) 0.195(2) 0.0631(15) Uiso 1.000000 GR
H26c H 0.184(3) 1.031(2) 0.2579(9) 0.0631(15) Uiso 1.000000 GR


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C2 1.723(4) . ?
Cl2 C3 1.730(4) . ?
N5 C9 1.331(4) . ?
N1 C9 1.340(4) . ?
N1 C8 1.332(4) . ?
N2 N3 1.352(4) . ?
N2 C9 1.353(4) . ?
N3 C7 1.285(5) . ?
N4 C8 1.321(5) . ?
C8 C7 1.458(5) . ?
C7 C1 1.490(5) . ?
C1 C2 1.405(5) . ?
C1 C6 1.392(5) . ?
C2 C3 1.384(5) . ?
C3 C4 1.391(5) . ?
C4 C5 1.380(5) . ?
C5 C6 1.391(5) . ?
O1 C22 1.246(4) . ?
O2 C22 1.280(4) . ?
N6 C10 1.424(5) . ?
N6 C16 1.360(5) . ?
C10 C11 1.394(6) . ?
C10 C15 1.400(5) . ?
C11 C12 1.376(6) . ?
C12 C13 1.385(6) . ?
C13 C14 1.386(6) . ?
C14 C15 1.404(5) . ?
C14 C24 1.517(5) . ?
C15 C23 1.503(6) . ?
C16 C21 1.416(5) . ?
C16 C17 1.419(5) . ?
C21 C22 1.514(4) . ?
C21 C20 1.392(5) . ?
C20 C19 1.385(5) . ?
C19 C18 1.401(5) . ?
C18 C17 1.367(5) . ?
O3 C25 1.436(5) . ?
C25 C26 1.498(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C9 116.8(3) . . ?
C9 N2 N3 121.5(3) . . ?
C7 N3 N2 118.2(3) . . ?
N1 C9 N5 120.7(3) . . ?
N2 C9 N5 116.7(3) . . ?
N2 C9 N1 122.5(3) . . ?
N4 C8 N1 119.8(3) . . ?
C7 C8 N1 120.1(3) . . ?
C7 C8 N4 120.2(3) . . ?
C8 C7 N3 120.7(3) . . ?
C1 C7 N3 115.6(3) . . ?
C1 C7 C8 123.5(3) . . ?
C2 C1 C7 118.8(3) . . ?
C6 C1 C7 121.9(3) . . ?
C6 C1 C2 119.1(3) . . ?
C1 C2 Cl1 119.1(3) . . ?
C3 C2 Cl1 120.8(3) . . ?
C3 C2 C1 120.0(3) . . ?
C2 C3 Cl2 119.9(3) . . ?
C4 C3 Cl2 119.6(3) . . ?
C4 C3 C2 120.4(3) . . ?
C5 C4 C3 119.8(3) . . ?
C6 C5 C4 120.3(3) . . ?
C5 C6 C1 120.3(3) . . ?
C16 N6 C10 124.1(3) . . ?
C11 C10 N6 119.2(3) . . ?
C15 C10 N6 120.6(3) . . ?
C15 C10 C11 120.2(3) . . ?
C12 C11 C10 120.6(4) . . ?
C13 C12 C11 119.6(4) . . ?
C14 C13 C12 120.8(4) . . ?
C15 C14 C13 120.0(3) . . ?
C24 C14 C13 119.3(4) . . ?
C24 C14 C15 120.7(4) . . ?
C14 C15 C10 118.7(3) . . ?
C23 C15 C10 121.1(3) . . ?
C23 C15 C14 120.1(4) . . ?
C21 C16 N6 122.0(3) . . ?
C17 C16 N6 120.3(3) . . ?
C17 C16 C21 117.7(3) . . ?
C22 C21 C16 122.0(3) . . ?
C20 C21 C16 119.4(3) . . ?
C20 C21 C22 118.6(3) . . ?
O2 C22 O1 123.0(3) . . ?
C21 C22 O1 120.4(3) . . ?
C21 C22 O2 116.6(3) . . ?
C19 C20 C21 122.2(3) . . ?
C18 C19 C20 118.5(3) . . ?
C17 C18 C19 120.7(3) . . ?
C18 C17 C16 121.5(3) . . ?
C26 C25 O3 112.4(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N5 H5b O1 0.8800 2.029(4) 2.890(4) 165.82(11) 2_566
N2 H2 O2 0.8800 1.775(4) 2.591(4) 153.12(12) 2_566
N4 H4b O3 0.8800 2.225(4) 2.818(4) 124.45(10) 1_655
N6 H6 O1 0.8800 1.979(4) 2.665(4) 133.79(12) .


_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.067
_oxdiff_exptl_absorpt_empirical_full_min 0.440
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_n01
_database_code_depnum_ccdc_archive 'CCDC 2380265'
loop_
_audit_author_name
_audit_author_address
'Zhengzheng Zhou'
;Southern Medical University
China
;
_audit_update_record             
;
2024-08-28 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_audit_creation_date             2024-08-28
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.01.12 svn.r2f8d729c for OlexSys, GUI svn.r6928)
;
_chemical_formula_moiety         'C9 H8 Cl2 N5, C14 H9 F3 N O2'
_chemical_formula_sum            'C23 H17 Cl2 F3 N6 O2'
_chemical_formula_weight         537.331
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
C 0.00313 0.00162 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.21560 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
Cl 0.14908 0.15974 11.46040 7.19640 6.25560 1.64550 0.01040 1.16620 18.51940
47.77840 -9.55740 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
F 0.01756 0.01033 3.53920 2.64120 1.51700 1.02430 10.28250 4.29440 0.26150
26.14760 0.27760 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.00304 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
N 0.00612 0.00332 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.52900 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'
O 0.01085 0.00610 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.25080 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Brennan, Cowan, Rev. Sci. Instrum., 1992, 63, 850'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   9.2015(9)
_cell_length_b                   11.6771(7)
_cell_length_c                   14.8897(10)
_cell_angle_alpha                73.590(6)
_cell_angle_beta                 76.902(7)
_cell_angle_gamma                88.509(6)
_cell_volume                     1493.5(2)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3159
_cell_measurement_temperature    149.9(2)
_cell_measurement_theta_max      27.4040
_cell_measurement_theta_min      2.4070
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55583
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.195
_exptl_crystal_description       block
_exptl_crystal_F_000             548.989
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_Laue_measured_fraction_full 0.9989
_diffrn_reflns_Laue_measured_fraction_max 0.9989
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            12436
_diffrn_reflns_point_group_measured_fraction_full 0.9989
_diffrn_reflns_point_group_measured_fraction_max 0.9989
_diffrn_reflns_theta_full        24.9984
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.27
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      149.9(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.9989
_diffrn_measured_fraction_theta_max 0.9989
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -13.00  85.00   1.00    4.00    --   11.90  57.00 -90.00   98
  2  ω     36.00  61.00   1.00    4.00    --   11.90 178.00  90.00   25
  3  ω    -15.00  79.00   1.00    4.00    --   11.90  77.00  30.00   94
  4  ω    -56.00  38.00   1.00    4.00    --   11.90 -57.00 120.00   94
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0583031000
_diffrn_orient_matrix_UB_12      -0.0407989000
_diffrn_orient_matrix_UB_13      -0.0019749000
_diffrn_orient_matrix_UB_21      -0.0523521000
_diffrn_orient_matrix_UB_22      -0.0482426000
_diffrn_orient_matrix_UB_23      0.0252466000
_diffrn_orient_matrix_UB_31      -0.0115842000
_diffrn_orient_matrix_UB_32      -0.0049442000
_diffrn_orient_matrix_UB_33      -0.0442816000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              10
_reflns_limit_h_min              -10
_reflns_limit_k_max              13
_reflns_limit_k_min              -13
_reflns_limit_l_max              17
_reflns_limit_l_min              0
_reflns_number_gt                4018
_reflns_number_total             5253
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine 1.5 (Bourhis et al., 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.9961
_refine_diff_density_min         -0.5958
_refine_diff_density_rms         0.0962
_refine_ls_d_res_high            0.8409
_refine_ls_d_res_low             8.9547
_refine_ls_goodness_of_fit_ref   1.0409
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    34
_refine_ls_number_parameters     347
_refine_ls_number_reflns         5253
_refine_ls_number_restraints     49
_refine_ls_R_factor_all          0.0878
_refine_ls_R_factor_gt           0.0720
_refine_ls_restrained_S_all      1.0358
_refine_ls_shift/su_max          -0.0009
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1159P)²+1.3377P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1978
_refine_ls_wR_factor_ref         0.2132
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2. Restrained distances
 F2-C10 \\sim F3B-C10
 with sigma of 0.02
 F3-C10 \\sim F1B-C10
 with sigma of 0.02
 F1-C10 \\sim F2B-C10
 with sigma of 0.02
3. Rigid bond restraints
 C5, C4
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C5, C6
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C5 \\sim C4: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.004 within 2A
C6: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.002 within
2A
Uanis(C5) = Uanis(C6)
5. Rigid body (RIGU) restrains
 F2, F3, F1, C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
 F3B, F2B, F1B, C10
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.002
6. Others
 Sof(F3B)=Sof(F1B)=Sof(F2B)=1-FVAR(1)
 Sof(F2)=Sof(F1)=Sof(F3)=FVAR(1)
7.a Aromatic/amide H refined with riding coordinates:
 N2(H2), N6(H6), C6(H6a), C19(H19), C12(H12), C22(H22), C21(H21), C14(H14),
 C20(H20), C16(H16), C15(H15), C5(H5), C4(H4)
7.b X=CH2 refined with riding coordinates:
 N5(H5a,H5b), N4(H4a,H4b)
;
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_group
Cl01 Cl -0.12754(12) 0.89096(8) 0.83422(7) 0.0457(3) Uani 1.000000 . . . .
Cl02 Cl 0.05384(15) 1.10080(9) 0.67053(9) 0.0632(4) Uani 1.000000 . . . .
O003 O 0.4075(2) 0.4897(2) 0.80994(16) 0.0288(5) Uani 1.000000 . . . .
O004 O 0.3675(3) 0.3330(2) 0.93835(16) 0.0330(6) Uani 1.000000 . . . .
N2 N -0.3346(3) 0.5303(2) 0.84618(19) 0.0257(6) Uani 1.000000 . . . .
H2 H -0.4187(3) 0.5057(2) 0.83763(19) 0.0309(7) Uiso 1.000000 R . . .
N3 N -0.1601(3) 0.5049(2) 0.94252(18) 0.0229(6) Uani 1.000000 . . . .
N1 N -0.2563(3) 0.6220(2) 0.77840(19) 0.0267(6) Uani 1.000000 . . . .
N5 N 0.0502(3) 0.6250(2) 0.88661(19) 0.0254(6) Uani 1.000000 . . . .
H5a H 0.0828(3) 0.5860(2) 0.93759(19) 0.0305(7) Uiso 1.000000 R . . .
H5b H 0.1047(3) 0.6845(2) 0.84276(19) 0.0305(7) Uiso 1.000000 R . . .
N4 N -0.3757(3) 0.3868(2) 0.99029(19) 0.0279(6) Uani 1.000000 . . . .
H4a H -0.4599(3) 0.3668(2) 0.97888(19) 0.0335(8) Uiso 1.000000 R . . .
H4b H -0.3499(3) 0.3481(2) 1.04389(19) 0.0335(8) Uiso 1.000000 R . . .
N6 N 0.2573(3) 0.4909(2) 0.67756(19) 0.0287(6) Uani 1.000000 . . . .
H6 H 0.3128(3) 0.5358(2) 0.69631(19) 0.0344(8) Uiso 1.000000 R . . .
F2 F 0.3622(12) 0.8499(11) 0.3445(9) 0.062(3) Uani 0.392(15) D U P 1
C8 C -0.0800(3) 0.5944(3) 0.8760(2) 0.0226(7) Uani 1.000000 . . . .
C18 C 0.1926(3) 0.3629(3) 0.8406(2) 0.0233(7) Uani 1.000000 . . . .
C9 C -0.2896(3) 0.4734(3) 0.9279(2) 0.0230(7) Uani 1.000000 . . . .
C23 C 0.3320(4) 0.3967(3) 0.8645(2) 0.0249(7) Uani 1.000000 . . . .
C17 C 0.1590(3) 0.4098(3) 0.7498(2) 0.0242(7) Uani 1.000000 . . . .
F1 F 0.5117(16) 0.7479(9) 0.2674(7) 0.067(3) Uani 0.392(15) D U P 1
C7 C -0.1329(4) 0.6560(3) 0.7904(2) 0.0247(7) Uani 1.000000 . . . .
C13 C 0.2798(3) 0.5109(3) 0.5780(2) 0.0254(7) Uani 1.000000 . . . .
C6 C 0.0271(4) 0.7363(4) 0.6231(2) 0.0376(6) Uani 1.000000 . U . .
H6a H 0.0239(4) 0.6600(4) 0.6125(2) 0.0451(7) Uiso 1.000000 R . . .
F3 F 0.5547(14) 0.7930(10) 0.3936(9) 0.074(3) Uani 0.392(15) D U P 1
C19 C 0.0913(4) 0.2815(3) 0.9113(2) 0.0292(7) Uani 1.000000 . . . .
H19 H 0.1136(4) 0.2490(3) 0.9725(2) 0.0350(9) Uiso 1.000000 R . . .
C12 C 0.3520(4) 0.6156(3) 0.5190(2) 0.0290(8) Uani 1.000000 . . . .
H12 H 0.3833(4) 0.6722(3) 0.5464(2) 0.0348(9) Uiso 1.000000 R . . .
C22 C 0.0231(4) 0.3759(3) 0.7365(2) 0.0288(7) Uani 1.000000 . . . .
H22 H -0.0024(4) 0.4097(3) 0.6764(2) 0.0345(9) Uiso 1.000000 R . . .
C21 C -0.0751(4) 0.2948(3) 0.8083(3) 0.0318(8) Uani 1.000000 . . . .
H21 H -0.1666(4) 0.2726(3) 0.7973(3) 0.0381(10) Uiso 1.000000 R . . .
C1 C -0.0465(4) 0.7559(3) 0.7133(2) 0.0295(8) Uani 1.000000 . . . .
C11 C 0.3799(4) 0.6396(3) 0.4204(3) 0.0358(9) Uani 1.000000 . . . .
C2 C -0.0362(4) 0.8674(3) 0.7274(2) 0.0338(8) Uani 1.000000 . . . .
C14 C 0.2371(4) 0.4273(3) 0.5367(3) 0.0348(8) Uani 1.000000 . . . .
H14 H 0.1879(4) 0.3538(3) 0.5762(3) 0.0418(10) Uiso 1.000000 R . . .
C20 C -0.0407(4) 0.2457(3) 0.8963(3) 0.0354(8) Uani 1.000000 . . . .
H20 H -0.1068(4) 0.1881(3) 0.9458(3) 0.0424(10) Uiso 1.000000 R . . .
C16 C 0.3363(4) 0.5581(4) 0.3796(3) 0.0429(10) Uani 1.000000 . . . .
H16 H 0.3543(4) 0.5753(4) 0.3116(3) 0.0514(12) Uiso 1.000000 R . . .
C15 C 0.2677(4) 0.4532(4) 0.4367(3) 0.0431(10) Uani 1.000000 . . . .
H15 H 0.2398(4) 0.3963(4) 0.4083(3) 0.0517(12) Uiso 1.000000 R . . .
C3 C 0.0446(4) 0.9615(3) 0.6532(3) 0.0398(9) Uani 1.000000 . . . .
C5 C 0.1018(4) 0.8326(3) 0.5531(3) 0.0376(6) Uani 1.000000 . U . .
H5 H 0.1478(4) 0.8225(3) 0.4920(3) 0.0451(7) Uiso 1.000000 R . . .
C4 C 0.1132(4) 0.9436(4) 0.5673(3) 0.0435(8) Uani 1.000000 . U . .
H4 H 0.1686(4) 1.0072(4) 0.5173(3) 0.0522(9) Uiso 1.000000 R . . .
C10 C 0.4514(5) 0.7563(4) 0.3585(3) 0.0515(9) Uani 1.000000 D U . .
F3B F 0.5024(10) 0.8235(6) 0.4079(4) 0.0685(18) Uani 0.608(15) D U P 2
F1B F 0.5668(8) 0.7531(5) 0.2914(5) 0.0623(17) Uani 0.608(15) D U P 2
F2B F 0.3458(8) 0.8226(7) 0.3210(7) 0.0694(19) Uani 0.608(15) D U P 2


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl01 C2 1.715(4) . ?
Cl02 C3 1.724(4) . ?
O003 C23 1.267(4) . ?
O004 C23 1.248(4) . ?
N2 H2 0.8800 . ?
N2 N1 1.336(4) . ?
N2 C9 1.361(4) . ?
N3 C8 1.319(4) . ?
N3 C9 1.337(4) . ?
N1 C7 1.278(4) . ?
N5 H5a 0.8800 . ?
N5 H5b 0.8800 . ?
N5 C8 1.314(4) . ?
N4 H4a 0.8800 . ?
N4 H4b 0.8800 . ?
N4 C9 1.301(4) . ?
N6 H6 0.8800 . ?
N6 C17 1.378(4) . ?
N6 C13 1.401(4) . ?
F2 C10 1.347(10) . ?
C8 C7 1.457(4) . ?
C18 C23 1.497(4) . ?
C18 C17 1.409(4) . ?
C18 C19 1.384(5) . ?
C17 C22 1.394(4) . ?
F1 C10 1.374(10) . ?
C7 C1 1.479(5) . ?
C13 C12 1.371(5) . ?
C13 C14 1.397(5) . ?
C6 H6a 0.9500 . ?
C6 C1 1.439(5) . ?
C6 C5 1.369(5) . ?
F3 C10 1.317(11) . ?
C19 H19 0.9500 . ?
C19 C20 1.379(5) . ?
C12 H12 0.9500 . ?
C12 C11 1.378(5) . ?
C22 H22 0.9500 . ?
C22 C21 1.375(5) . ?
C21 H21 0.9500 . ?
C21 C20 1.378(5) . ?
C1 C2 1.385(5) . ?
C11 C16 1.377(6) . ?
C11 C10 1.483(5) . ?
C2 C3 1.402(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.395(5) . ?
C20 H20 0.9500 . ?
C16 H16 0.9500 . ?
C16 C15 1.352(6) . ?
C15 H15 0.9500 . ?
C3 C4 1.363(6) . ?
C5 H5 0.9500 . ?
C5 C4 1.381(6) . ?
C4 H4 0.9500 . ?
C10 F3B 1.371(8) . ?
C10 F1B 1.290(7) . ?
C10 F2B 1.348(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N1 N2 H2 118.70(15) . . ?
C9 N2 H2 118.70(17) . . ?
C9 N2 N1 122.6(3) . . ?
C9 N3 C8 117.6(3) . . ?
C7 N1 N2 118.4(3) . . ?
H5b N5 H5a 120.0 . . ?
C8 N5 H5a 120.0 . . ?
C8 N5 H5b 120.0 . . ?
H4b N4 H4a 120.0 . . ?
C9 N4 H4a 120.0 . . ?
C9 N4 H4b 120.0 . . ?
C17 N6 H6 115.93(16) . . ?
C13 N6 H6 115.93(17) . . ?
C13 N6 C17 128.1(3) . . ?
N5 C8 N3 119.1(3) . . ?
C7 C8 N3 120.5(3) . . ?
C7 C8 N5 120.4(3) . . ?
C17 C18 C23 123.3(3) . . ?
C19 C18 C23 118.4(3) . . ?
C19 C18 C17 118.3(3) . . ?
N3 C9 N2 120.8(3) . . ?
N4 C9 N2 117.7(3) . . ?
N4 C9 N3 121.5(3) . . ?
O004 C23 O003 122.8(3) . . ?
C18 C23 O003 118.8(3) . . ?
C18 C23 O004 118.4(3) . . ?
C18 C17 N6 120.0(3) . . ?
C22 C17 N6 121.4(3) . . ?
C22 C17 C18 118.6(3) . . ?
C8 C7 N1 120.1(3) . . ?
C1 C7 N1 117.4(3) . . ?
C1 C7 C8 122.5(3) . . ?
C12 C13 N6 118.0(3) . . ?
C14 C13 N6 123.0(3) . . ?
C14 C13 C12 119.0(3) . . ?
C1 C6 H6a 121.5(2) . . ?
C5 C6 H6a 121.5(2) . . ?
C5 C6 C1 117.0(4) . . ?
H19 C19 C18 118.71(19) . . ?
C20 C19 C18 122.6(3) . . ?
C20 C19 H19 118.7(2) . . ?
H12 C12 C13 119.59(19) . . ?
C11 C12 C13 120.8(3) . . ?
C11 C12 H12 119.6(2) . . ?
H22 C22 C17 119.2(2) . . ?
C21 C22 C17 121.6(3) . . ?
C21 C22 H22 119.2(2) . . ?
H21 C21 C22 120.0(2) . . ?
C20 C21 C22 120.1(3) . . ?
C20 C21 H21 120.0(2) . . ?
C6 C1 C7 119.3(3) . . ?
C2 C1 C7 120.6(3) . . ?
C2 C1 C6 120.0(3) . . ?
C16 C11 C12 120.3(4) . . ?
C10 C11 C12 119.6(4) . . ?
C10 C11 C16 120.1(4) . . ?
C1 C2 Cl01 119.8(3) . . ?
C3 C2 Cl01 120.3(3) . . ?
C3 C2 C1 119.9(3) . . ?
H14 C14 C13 120.4(2) . . ?
C15 C14 C13 119.2(4) . . ?
C15 C14 H14 120.4(2) . . ?
C21 C20 C19 118.8(3) . . ?
H20 C20 C19 120.6(2) . . ?
H20 C20 C21 120.6(2) . . ?
H16 C16 C11 120.2(2) . . ?
C15 C16 C11 119.6(3) . . ?
C15 C16 H16 120.2(2) . . ?
C16 C15 C14 121.1(4) . . ?
H15 C15 C14 119.5(2) . . ?
H15 C15 C16 119.5(2) . . ?
C2 C3 Cl02 119.6(3) . . ?
C4 C3 Cl02 120.2(3) . . ?
C4 C3 C2 120.2(4) . . ?
H5 C5 C6 118.5(2) . . ?
C4 C5 C6 123.0(3) . . ?
C4 C5 H5 118.5(2) . . ?
C5 C4 C3 119.8(4) . . ?
H4 C4 C3 120.1(2) . . ?
H4 C4 C5 120.1(2) . . ?
F1 C10 F2 104.0(7) . . ?
F3 C10 F2 103.3(7) . . ?
F3 C10 F1 110.2(7) . . ?
C11 C10 F2 117.0(6) . . ?
C11 C10 F1 109.7(6) . . ?
C11 C10 F3 112.1(6) . . ?
F3B C10 F2 79.4(6) . . ?
F3B C10 F1 128.6(7) . . ?
F3B C10 F3 26.8(4) . . ?
F3B C10 C11 113.8(4) . . ?
F1B C10 F2 119.0(7) . . ?
F1B C10 F1 30.1(5) . . ?
F1B C10 F3 81.0(6) . . ?
F1B C10 C11 116.8(4) . . ?
F1B C10 F3B 103.1(5) . . ?
F2B C10 F2 24.9(5) . . ?
F2B C10 F1 86.8(6) . . ?
F2B C10 F3 126.8(6) . . ?
F2B C10 C11 107.8(5) . . ?
F2B C10 F3B 104.2(5) . . ?
F2B C10 F1B 110.4(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl01 C2 C1 C7 -1.3(3) . . . . ?
Cl01 C2 C1 C6 178.6(3) . . . . ?
Cl01 C2 C3 Cl02 0.9(3) . . . . ?
Cl01 C2 C3 C4 -177.9(3) . . . . ?
Cl02 C3 C2 C1 178.8(3) . . . . ?
Cl02 C3 C4 C5 -178.2(3) . . . . ?
O003 C23 C18 C17 16.3(3) . . . . ?
O003 C23 C18 C19 -163.6(3) . . . . ?
O004 C23 C18 C17 -164.9(3) . . . . ?
O004 C23 C18 C19 15.2(3) . . . . ?
N2 N1 C7 C8 0.6(3) . . . . ?
N2 N1 C7 C1 178.6(3) . . . . ?
N2 C9 N3 C8 1.4(3) . . . . ?
N3 C8 C7 N1 -1.4(3) . . . . ?
N3 C8 C7 C1 -179.3(3) . . . . ?
N1 C7 C8 N5 176.7(3) . . . . ?
N1 C7 C1 C6 -71.2(3) . . . . ?
N1 C7 C1 C2 108.7(3) . . . . ?
N5 C8 C7 C1 -1.3(4) . . . . ?
N6 C17 C18 C23 0.2(4) . . . . ?
N6 C17 C18 C19 -179.9(3) . . . . ?
N6 C17 C22 C21 179.8(3) . . . . ?
N6 C13 C12 C11 178.9(3) . . . . ?
N6 C13 C14 C15 -178.2(3) . . . . ?
F2 C10 C11 C12 -81.2(8) . . . . ?
F2 C10 C11 C16 96.2(8) . . . . ?
C8 C7 C1 C6 106.8(3) . . . . ?
C8 C7 C1 C2 -73.4(3) . . . . ?
C18 C17 C22 C21 -2.6(4) . . . . ?
C18 C19 C20 C21 -1.6(4) . . . . ?
C17 C22 C21 C20 0.6(4) . . . . ?
F1 C10 C11 C12 160.7(7) . . . . ?
F1 C10 C11 C16 -21.9(8) . . . . ?
C7 C1 C6 C5 178.0(3) . . . . ?
C7 C1 C2 C3 -179.2(3) . . . . ?
C13 C12 C11 C16 -0.5(4) . . . . ?
C13 C12 C11 C10 176.9(3) . . . . ?
C13 C14 C15 C16 -0.7(4) . . . . ?
C6 C1 C2 C3 0.7(4) . . . . ?
C6 C5 C4 C3 -1.9(4) . . . . ?
F3 C10 C11 C12 37.9(8) . . . . ?
F3 C10 C11 C16 -144.7(7) . . . . ?
C19 C20 C21 C22 1.5(4) . . . . ?
C12 C11 C16 C15 -0.9(4) . . . . ?
C12 C11 C10 F3B 8.8(6) . . . . ?
C12 C11 C10 F1B 128.8(6) . . . . ?
C12 C11 C10 F2B -106.3(5) . . . . ?
C1 C2 C3 C4 -0.0(4) . . . . ?
C11 C16 C15 C14 1.5(4) . . . . ?
C2 C3 C4 C5 0.6(4) . . . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 -0.293 0.000 -0.449 421.7 106.3 ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 2.170
_oxdiff_exptl_absorpt_empirical_full_min 0.542
loop_
_restr_equal_distance_atom_site_label_1
_restr_equal_distance_atom_site_label_2
_restr_equal_distance_site_symmetry_2
_restr_equal_distance_class_id
F2 C10 1 1
F1 C10 1 3
F3 C10 1 2
F3B C10 1 1
F1B C10 1 2
F2B C10 1 3

loop_
_restr_equal_distance_class_class_id
_restr_equal_distance_class_target_weight_param
_restr_equal_distance_class_average
_restr_equal_distance_class_esd
_restr_equal_distance_class_diff_max
1 0.0200 1.3592 0.0121 0.0121
2 0.0200 1.3038 0.0134 0.0134
3 0.0200 1.3611 0.0127 0.0127

loop_
_restr_RIGU_atom_site_label_1
_restr_RIGU_atom_site_label_2
_restr_RIGU_target_weight_param
_restr_RIGU_U13_diff
_restr_RIGU_U23_diff
_restr_RIGU_U33_diff
F2 F1 0.002000 -0.015349 -0.011625 -0.005574
F2 F3 0.002000 -0.012053 0.005435 -0.000081
F2 C10 0.001000 0.001754 0.001525 0.000852
F1 F3 0.002000 0.016804 0.031125 -0.013845
F1 C10 0.001000 -0.001059 0.000044 0.000252
F3 C10 0.001000 0.000260 -0.001439 0.001124
C10 F3B 0.001000 -0.002906 0.002543 0.000411
C10 F1B 0.001000 0.001030 -0.002587 -0.001002
C10 F2B 0.001000 0.001443 -0.001779 -0.000639
F3B F1B 0.002000 0.014601 -0.015097 0.005034
F3B F2B 0.002000 -0.024957 0.000825 0.011291
F1B F2B 0.002000 -0.023703 -0.014672 -0.008861

loop_
_restr_U_rigid_atom_site_label_1
_restr_U_rigid_atom_site_label_2
_restr_U_rigid_target_weight_param
_restr_U_rigid_U_parallel
_restr_U_rigid_diff
C5 C4 0.0100 0.0539 -0.0031

loop_
_restr_U_similar_atom_site_label_1
_restr_U_similar_atom_site_label_2
_restr_U_similar_weight_param
C5 C4 0.0020

